Winchester one shots
by fireylillies
Summary: One shots involving your favorite Supernatural characters. Destial. Sassy. Wincest. Whatever you want it will be written. Not all Smut but it happens. Leave a PM. or Review of what you want and i'll write it. Can include Crossovers, A.U,/ A.W and anything else you want. Warning: Lots of sex, gay sex and probably incest at some point. Enjoy and Review!
1. Chapter 1: Solo Dean

This is the first of many possiable chapters. If theres anything you want to see happen let me know. Smut. Not smut. Gay sex. Crossovers. Anything you name it it will happen. Review or PM with comments or anything xoxo

**Summary: Dean finds himself alone on a hunt after Sam is badly hurt and resting. After he is taken captive Dean is rescued by a sexy Demon who is an old friend. Smut. Rating-M**

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Dean watched as she moved, there was something in her movements that showed she wasn't human. The way she fought, the way she moved. There was a glint in her hard, demonic, black eyes that had Dean curious. She brought her long curved blade into the chest of the demon that Dean had been hunting, sending it back to hell.

She paused for a moment, trying to hear any movement. When she decided that there was nothing there she turned to Dean who was tied to a rough metal chair by rusty chains. "Dean," She said, pausing to break the chains, "Winchester. Fancy meeting you here."

"Do I know you?" Dean drawled eyeing the woman who just saved his ass from a five on one demon fight.

"No," She admitted, "But I know you. We all do. I just don't hate you. My name is Cassi," She stuck out her hand to Dean, "I was sent to give you a hand. Since Sam is taking a break."

Dean looked her over once more, Sam had decided to take short break from hunting after having to get a bullet removed from his head, and one from around his heart. Dean had encouraged this break, making Sam stay in a small apartment and just do research for Dean.

"Who sent you?"

Cassi smiled slightly, "John and Jo did, they insisted that I had to go make sure you didn't kill yourself in a crazy ass hunt like this."

Dean paused to take in the woman before him. She was tall and had amazing curves. Her hair was dark auburn and waved down her back and shoulders, she had big green eyes that captivated Dean when they weren't covered by the black of being a demon. "Will you accept my help Winchester?"

"Who's to say you won't just fuck me over?" Dean asked, standing up, he rubbed his sore wrists, which were bloody from the chains he had struggled against.

Cassi smiled, "I'm offended Dean. Don't you remember me?" She purred, "Lets see, May 22 to the 29th, 2014. Does that week ring any bells?"

Dean thought back to May, 2014. He had been in the hospital because he got pretty roughed up. One of the nurses had been a hunter in her spare time. Her name was Cassiopeia and she spent a lot of time with Dean, even breaching hospital code to sleep with him multiple times. She wanted to go hunt with Dean and Sam but she was consumed by a black smoke that Dean found out later to be a very old powerful demon. He thought she'd be gone forever.

"Is that your old meat suit?" Dean asked with a quirked smile.

Cassi laughed a bit at that, "Yeah I put in a special request for it," She smiled.

Dean looked at her, before he smiled a bit. "Wanna get outta here?" Cassi smiled and nodded.

She and dean discarded the bodies before leaving in the Impala, dean driving. Dean and Cassi went on a few more hunts, tracking demons for a few weeks, while Sam was recovering. Dean adjusted to hunting with someone who was supernatural rather well. Cassi and Dean worked well together, Dean felt like she was almost human, that she wasn't completely demon.

Sam wasn't so thrilled that Dean was hunting with a demon, not after Ruby. But if Cassi wanted Dean dead she could have not saved him that day at the hunt where he was outnumbered.

Sam expressed his dislike on the phone while Cassi was out to get food.

"I don't like it Dean, what if she has an alterior motive?" Sam asked for the hundreth time.

Dean sighed, "Don't worry Sammy, you'll be back soon," Dean said, "Just heal. I'll be fine."

Dean could see Sam now, sitting on a hard kitchen chair rubbing the bridge of his nose and sighing at his older brother. "Okay Dean," Sam said, "I'll see you soon right?"

"Course' Sammy. Since your cleared for physical activity i'll be picking you up in a few days when get to L.A."

Dean hung up just as the Motel door opened. "We're leaving to get Sam tomorrow aren't we?" Cassi asked when she locked the door behind her. Dean opened his mouth to say something but was cut off, "He doesn't like me. I'll drive with you to California, but i'll depart from there. Since Sam doesn't like me. I'll always be a call away though."

Dean walked over to where the brunette stood, he put one hand on the back of her head and curled his fingers around her hair. In one swift motion he brought her to him and kissed her full on the lips. He'd wanted to do so for a long while but never had the guts.

Cassi reacted right off the bat and wraped her arms around Dean's shoulders, Dean's hands drop to Cassi's ass, at first cupping it, then pulling Cassi up so her legs were wraped around his waist. Dean brought Cassi to the bed and gently threw her down onto the bed.

Dean pulled off his shirt and slid off his belt. Cassi quickly removed her shirt and jeans. Revealing matching black lace underwear. Dean smiled a cocky smile, "Hotter then I remember," He said appraising her curves, her full chest, her grab-able hips with lustful eyes.

"Stop staring and fuck me Winchester," Cassi said impatiently.

Hasty Dean removed his jeans and slid out of his boxers. He fell to Cassi's lips kissing her had and biting at the bottom one with hard teeth. HIs hands slid to her back and quickly dealt with her bra, he slid down the bed and squeezed her breasts together before attacking the left one with kisses and light nibbles. He made sure each got enough attention before sliding down the bed further, bringing the black lace down with him.

"Well aren't we wet," Dean said before he inserted a finger inside of her. Cassi arched her back as Dean's tongue swirled around her clit. She moaned a happy giggle before she pulled Dean up to her lips. "Come on now Sexy. We've waited long enough, get inside of me," Cassi said with serious eyes.

Her eyes were dark green but glinted with black, normally that would have bothered Dean but he was too consumed by lust to worry that he was about to have sex with a Demon.

Dean did as she asked and entered her, Cassi arched her back at the sensation, her nails dug into Dean's back and she brought her lips to his skin. Dean trusted in and out of Cassi, who was moaning louder with every coming thrust. One thing Dean had always liked about the georgus bombshell of a woman was that she was a screamer, let you know when you were doing a good job.

Cassi brought her nails hard into Deans back, scratching as he thrust into her, Dean brought his mouth to the Demon womans neck and took the soft skin into his mouth. Dean continued to thrust until he felt Cassi constricting around him, her walls getting tighter, that sensation sent him over the edge, they rode out their orgasms together.

Dean rolled off of Cassi and pulled her into his side, she used him as a pillow and they laid there together. Dean falling asleep very fast.

When Dean woke up Cassi was on the phone, "No I didn't kill him Sam, he's asleep. Like he has been for the last five phone calls you made," Cassi said sounding annoyed. Dean stood up and took his phone from Cassi.

"Sam, I am fine. I'm taking a shower, then leaving. I'll be there soon. Don't get your panties in a knot."

Dean could practically hear Sam roll is eyes, "Fine, drive fast."

"Don't I always?" Dean asked, a smirk in his tone.

Once he hung up Dean looked at Cassi, "Shower. Now."

Cassi giggled and stripped off as she hurried to the small glass shower. She turned on the warm water and waited for Dean. When he came in he was fully erect and lust filled his eyes. He grabbed Cassi by a handful of dark Auburn hair and kissed her fiercely. With one hand he took both of hers and pinned them behind her back before he pushed Cassi up against the glass shower wall.

Dean entered her from behind and started to massage her breasts as he pushed in and out of her. Dean fucked Cassi against the glass wall of the shower, his motions were hard and fast, and Cassi was moaning harder with each coming pump.

Dean and Cassi once again finished together, then cleaned themself off using the bland smelling Motel soap. Once they were out and dressed Dean gathered his things so he could go to Sam.

It only took Dean two days to get to California, once he got there he and Cassi parted, she requested to be dropped off at a bar in the sketchier side of town before Dean went to Sam's apartment.

When Sam opened the door he looked Dean over, "You slept with her didn't you?" Sam asked.

Dean rolled his eyes before hugging his younger brother, "I missed you."

"No chick flick moments, Jerk," Sam said as he excepted his brothers hug.

"Can If I wanted, Bitch."

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**Hope you enjoyed. Please P.M or Review. Favorite and Follow. It makes me happy. xoxo enjoy.**

** F.L, Carry on my wayward sons. **


	2. Chapter 2: Supernatural the band

**Summary: Dean, Sam, Bobby and Castiel are members of an internationally famous rock band called Supernatural. Dean and Sam are known for giving out backstage passes to girls they take a liking too. Rayn and Mia are invited back for some fun. Smut. rating M**

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I took my best friends hand and started to weave my way through the packed crowd. Using m free elbow to dig through the people, after a bit of squeezing and pushing I reached the guard bar that stood between the giant crowd and the stage that would soon hold my favorite band; Supernatural.

"I must say i'm impressed," Mia said looking at the stage with a smile, "Good job Rayn. You got us in the best place."

I looked down at my best friend, she was small and short, she wore black rimmed glasses that hid hazel eyes, her face was splashed with freckles and her hair was red, making her ginger. Mia was very pretty, small, cute. Very cuddly looking. I on the other hand wasn't so soft. I was taller then her 5'0 by at least six inches, with long black hair and green eyes I was pretty as well. I knew I was very pretty and I used my looks to my advantage.

"I just hope he see's us," I said with a smirk.

The he in question was Dean Winchester as he went by for his stage name, he was the lead singer of Supernatural. Sam Winchester was one of the guitar players and back up singer. Bobby Singer was the drummer and Castiel Winchester was the other guitarist. They were the hottest rock band i'd ever heard of.

Mia rolled her eyes at me, "Theres so many pretty girls here," She said, "We're just two."

"Oh come off it," I said, "We're both really pretty. We might just attract some attention. Dean is known for handing out backstage passes to the girls he likes," I reminded her.

Mia nodded allowing that, I smiled slightly and pulled out my phone, taking a picture of Mia and I standing in front of the crowd. After a little while the first band came on, a small one called Lilith and the demons. The main girl was pretty and sounded okay, not great. After her the second band came on, they were actually pretty good.

The Hunters were a new band that was getting more famous and had some pretty good songs. Just before their last song they said for the pretty girls to get up on shoulders and catch Supernatural t-shirts. I looked at Mia and bent down so she could get up on my shoulders. She squealed and giggled as I stood up, I made eye contact with the lead singer of the band and winked. Mia must have done the same with the drummer because suddenly two black t-shirts decorated with devils traps and their logo on it flew into Mia's hands. I reached my hand up for a high five.

Mia stayed up on my shoulders for a bit before I let her down, we both fixed out hair and slipped on the t-shirts. Of course we both owned ones of our own, but these ones looked good over our skirts. As the sun finally set Supernatural reached the stage. Everyone screamed together.

Mia and I both reached our hands out towards the stage. As he scanned the crowd I could have sworn Dean's eyes met mine, the bright green that were so well known on places like Tumblr and Redit.

"Are you guys ready for this shit?" Dean yelled out with a quirked smile, Once the screaming died down Dean looked out, "See a lot of pretty ladies out there, this is why I love this fucking place. Great alcohol, friendly people and hot women," Dean let out a woop and the crowed yelled back.

Bobby, Castiel and Sam started to play at the same time, Dean joining in after a moment. I looked down at Mia, who's face was a lite with excitement. We sang along with Dean as he sang. He was hotter in person then anything. I'd been to one of his concerts before but Mia had never been this close. After a few songs he spoke some more, every second word out of his mouth was a curse. He did a few more songs and as he was singing he jumped down off the stage and started to run along the barrier, causing everyone to scream. All the girls mast to where he ran. He moved up to the barrier where Mia and I were standing. He pressed something into my hand and ran off before anyone could notice anything.

I looked at Mia who squeezed. In my hand were two back stage passes. Our eyes looked up to the stage, Dean met my eyes and winked. He was so known for getting with fans. "And the benefits of being pretty," I said with a smirk at my friend. Mia nodded in agreement and turned her attention back to the men on stage. I did the same, feeling a new sence of excitement. Dean Winchester, of Supernatral the biggest rock band out there had decided to invite me and my best friend back stage. Out of the thousands of girls here, us. I was beaming as the concert came to an end.

We made our way to the side of the stage, security stopped us but once he checked our passes he let us through. We walked behind the stage, girls who also had passes were taking photos and getting autographs with the band so Mia and I sat on the stairs to the stage and waited for the band to be done with the other fans. As soon as they were done with those girls Dean and Sam made their way over to where Mia and I sat.

"Who might you lovely ladies be?" Dean asked with a quirked smile.

"I am Rayn Campbell and this is my friend Mia Donve," I said, extending my hand to Dean.

The two brothers exchanged a glance before looking back at us, "We've met before," Dean said eyeing me.

"Why yes we have. Summer of '09, your first concert here. I had passes then," I winked.

"Oh yes I remember that," Dean said, "Would you ladies like to come back to our bus. Cass and Bobby have plans of their own out on the town and we wouldn't want to be lonely. You ladies don't have any place to be do you?"

I looked at Mia who was still shocked, "Nope, neither of us have classes tomorrow so we're all yours. Isn't that right Mia?" I asked elbowing my friend.

"Yeah! No plans, we're good," She said in a breathless tone. Sam and Mia started walking back towards the bus but Dean hung back to walk with me.

"You look good," He said appraising me, "So do you," I flashed back.

Dean let out a low growl, "We'll have some fun tonight," He said quietly. I giggled and nodded. I was going to sleep with Dean Winchester, international star.

Sam, Dean, Mia and I sat in their tour bus, a small house on wheels. I'd never seen the inside but it was nice, very clean. Probably for when the boys brought back girls. Dean had his arm draped around my shoulders and was looking at my eyes as we talked, Mia and Sam were deep in conversation. I knew that Dean had always been Mia's favorite but now that Sam was giving her all this attention she was eating it up. Sam was hot, no one would deny him that.

After a little while Dean asked if I wanted to see the back of he bus, meaning he was giving Mia and Sam space, as well as us being alone. As soon as he closed the door to a bedroom looking place Dean's lips were on mine.

I was all for one night stands and had nothing against fucking Dean Winchester in his tour bus, it had been a fantasy of every fan girl for the last six years. Dean hurried to pull off the band t-shirt I wore, my hands slid his black shirt off.

Dean picked me up, so I could wrap my legs around his waist, "You are so beautiful," Dean growled in between kisses. He pressed my back against the wall and kissed me forcefully. I kicked off my shoes and let my hands wander to his belt. Dean laughed before moving us over to the bed, he slid off his pants and unziped the zipper at my side removing the black dress I wore In one swift movement. Dean laid down beside me and pulled me on top of him. I could feel his arousal pressing into my hips and ground down, gaining a throaty moan from the singer.

Dean undid my bra quickly and squeezed my breasts before bringing me back to his lips. As we kissed I moved my hips down on his arousal, one of his hands traced my body while the other reached behind him for condoms I presumed. Dean rolled us over so I was on my back. In one swift movement he removed both of our underwear. As he fiddled with the condom he slid a finger into me.

"Looks like I'm not the only excited one," Dean said with a smile. He brushed his thumb over my clit and smirked at my moan. "You look so sexy when you moan, Rayn," Dean said with a smile.

Dean positioned himself so he was at my entrance, he kissed me as he thrust in. I couldn't help but buck my hips. Dean developed a rhythm. I kissed his neck as he thrust into me. Moving faster as time went on. With each thrust I moaned, Dean knew what he was doing. He continued to thrust into me as I rode out an orgasm. "Oh you like that don't you," Dean whispered into my ear. I moaned something that vaguely sounded like a yes. Dean pulled out and flipped me over. I smirked as i slid my knees up the bed, pointing my ass towards him.

"Well that's a real nice view," Dean said, I caught a hint of a drawl in his deep voice as he entered me from behind.

I let out a moan of surprise as a hand slapped against the soft skin of my bare ass. "Oh you like that don't you," Dean muttered.

"Yes I do," I said in a higher pitch then I was used to. Deans hand met my skin in the same place, I assumed there would be a mark there. Dean grabbed a handful of my black curls and pulled me up so my back was straight, kissing my neck. "You liked to be fucked like a little whore don't you?" Dean asked smile in his voice, he asked before nipping at my ear.

"Oh hell yeah," I said as Dean pushed me back to the bed. After a few more thrusts Dean pulled out and flopped down on the bed after tying up the condom. "I must say you're good Dean," I said as he pulled me into his chest.

"I try, baby. I try," Dean said, "What are you doing with your life Rayn? decides sleeping with random rockstars?"

"Im in med school, wanna be a psychiatrist. I want to help people," I said quietly. Dean looked at me with a cocked eyebrow.

"More then just a pretty face and a nice body I see," Dean said. I smiled and closed my eyes, Dean did the same.

Mia's Point of View.

Sam brought his lips roughly to mine, kissing me fiercely. I responded by sliding over to straddle his waist. His hands went to the bottom of my dress and took it and the t-shirt off in one swift motion. I undid his pants as I slid off his shirt. Sam uncliped my bra swiftly before standing up, me in his arms. He removed his pants and set me on my feet, he removed my underwear in one swift flick.

Sam reached into his pants pocket and pulled out a condom, he put it on before picking me back up. I wrapped my legs around him and kissed him. I found it a bit hard to believe that I was about to have sex with Sam Winchester. After a moment I slid myself down onto Sam's length. Sam pressed my back against a wall and started to thrust into me, kissing me as he did.

Sam thrust fast and hard, stifling my moans with kisses. After a short while I felt myself getting closer to my finish, I bit into Sam's lip to stifle my cry of pleasure. He continued to fuck me through my orgasm, almost imminently after I finished I started to climax again which set Sam off, he finished then set me down on the couch, he tied off the condom and pulled me down the hall. Sam laid down on a bed and pulled me into his arms.

"What life path are you headed down?" Sam asked as we laid there.

"Med school, with Rayn. I'm going to be a baby doctor," I said sleepily.

I could hear Sam chuckle, "Go to sleep," He muttered. I closed my eyes and did as he said. I just had a one night stand with Sam Winchester, and I couldn't have been more happy about it.

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**Hope you enjoyed. **

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** xoxo. F.L, Carry on My wayward sons**


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